Potassium Carbonate → HCID 86700253, compound

HRID 879445Notes

Reaction equation

HRID 879445 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][N:6]2[CH:11]=[C:10](B(O)O)[CH:9]=[N:8][C:7]=12)[CH3:2].O1CCOCC1.[C:21]([O:25][C@@H:26]([C:32]1[C:47]([CH3:48])=[CH:46][C:35]2[N:36]=[C:37]([C:39]3[CH:44]=[CH:43][N:42]=[C:41](Cl)[CH:40]=3)[S:38][C:34]=2[C:33]=1[C:49]1[CH:54]=[CH:53][C:52]([Cl:55])=[CH:51][CH:50]=1)[C:27]([O:29][CH2:30][CH3:31])=[O:28])([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:21]([O:25][C@@H:26]([C:32]1[C:47]([CH3:48])=[CH:46][C:35]2[N:36]=[C:37]([C:39]3[CH:44]=[CH:43][N:42]=[C:41]([C:10]4[CH:9]=[N:8][C:7]5[N:6]([N:5]=[CH:4][C:3]=5[CH2:1][CH3:2])[CH:11]=4)[CH:40]=3)[S:38][C:34]=2[C:33]=1[C:49]1[CH:50]=[CH:51][C:52]([Cl:55])=[CH:53][CH:54]=1)[C:27]([O:29][CH2:30][CH3:31])=[O:28])([CH3:22])([CH3:23])[CH3:24]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 86700142(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetateHCID 86700254HCID 86700254, compound

Product 1

HCID 86700253HCID 86700253, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of the above crude 3-ethylpyrazolo[1,5-a]pyrimidin-6-ylboronic acid in dioxane (˜0.18M, 0.68 mL, 0.123 mmol) was added (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (50 mg, 0.0944 mmol), Pd(PPh3)4 (11 mg, 0.0094 mmol) and 2M potassium carbonate (0.19 mL, 0.378 mmol) was heated in a microwave at 110° C. for 1 h. Reaction mixture was stored overnight at rt, diluted with ethyl acetate and washed with brine, dried (MgSO4), filtered, concentrated and purified by CombiFlash (0 to 40% EtOAc/Hex) to give product. LCMS-ESI+: calc'd for C35H35ClN5O3S: 640.2 (M+H+); Found: 640.3 (M+H+).

Workup

  1. customReaction mixture
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by CombiFlash (0 to 40% EtOAc/Hex)
  7. customto give product

Sources & evidence

ORD record
ord-8e5536f3c03545139d7b28458f4b4327
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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